Gaf Corporation

Louis Schneider

David E Graham

Bruce M Resnick

David E Graham, Deceased

Fidelity Union Trust Company, Executor

Herbicidal N-(haloacetyl-N-(N'-methylenepyrrolidonyl)-2-alkoxyanilines are provided in this invention having the formula: ##STR1## where R is alkyl of 1-6 carbon atoms, R' is hydrogen or lower alkyl of 1-3 carbon atoms, and X is halogen. The compounds of the present invention show good herbicidal activity against grassy weeds.

Herbicidal N-(haloacetyl)-N-(N'-methylenepyrrolidonyl)-2-alkoxyanilines

The use of N-(haloacetyl)-N-(N'-methylenepyrrolidonyl)-2-alkoxyaniline compounds for regulating the natural growth or development of plants, particularly turfgrasses, is described herein.

Method of plant growth regulation

Herbicidal compounds having the formula: ##STR1## where R is alkyl having 1-6 carbon atoms, alkenyl having 2-6 carbon atoms, cycloalkyl having 4-6 carbon atoms, unsubstituted or substituted with alkyl of 1-4 carbon atoms, or alkyleneoxyalkyl of 2-8 carbon atoms,

Herbicidal

The present invention provides an improved process of isolating purified, free 1-(alkoxyphenyl)-5-(phenyl)biguanide compounds, from a crude acid reaction mixture thereof. The compounds have the formula: ##STR1## where R is alkyl, linear of branched, having from 1-14 carbon atoms, and are useful as agricultural fungicides. The process comprises neutralizing the crude acid reaction mixture with aqueous base to precipitate the crude, free biguanide, filtering, slurrying the precipitate with a purification solvent which is an aliphatic hydrocarbon straight chain or branched, having from 5-10 carbon atoms, or mixtures thereof, filtering the slurry, and, drying the solid. Hexane is preferred as the purification solvent.

Process for isolating 1-(alkoxyphenyl)-5-(phenyl)biguanide compounds

The present invention provides an improved method of making 1-(alkoxyphenyl)-5-(phenyl)biguanide compounds which are useful as agricultural fungicides, having the formula: ##STR1## where R is alkyl, linear of branched, having from 1-14 carbon atoms; and acid addition salts thereof. The method comprises the steps of (a) alkylating a nitrophenol with a suitable alkyl halide in a reaction solvent to form an alkoxynitrobenzene intermediate, (b) reducing the nitro group of the itermediate in situ by catalytic hydrogenation to form an alkoxyaniline, and (c) condensing the alkoxyaniline with phenyldicyandiamide to form the desired biguanide as the acid addition salt. The invention also includes a novel isolation and purification procedure for obtaining purified biguanide acid addition salts and purified free biguanide base.

Method of making 1-(alkoxyphenyl)-5-(phenyl)biguanide compounds which

This invention relates to an improved process for making N-(N'-methylenepyrrolidonyl)-2-substituted anilines which are useful intermediates in the synthesis of agricultural herbicides. This process of the invention comprises reacting a 2-substituted aniline with N-chloromethylpyrrolidone at about room temperature in the presence of an acid acceptor. Such room temperature alkylation of the aniline prevents excessive side reactions, particularly with a substituent in the 2-position of the aniline, such as an alkenyl group, which is sensitive to alkylating agents which require excessive heating to effective the condensation reaction.

Process for making N-(N'-methylenepyrrolidonyl)-2-substituted anilines

This invention relates to a process for making N-(N'-methylenepyrrolidonyl)-2-substituted anilines in high yield. The products are useful intermediates in the synthesis of herbicides. The process comprises reacting substantially equivalent molar concentrations of a 2-substituted aniline, as defined herein, with N-methylolpyrrolidone in an aromatic hydrocarbon solvent in the absence of an acid or base catalyst at a reflux temperature of 80.degree.-140.degree. C. while simultaneously and continuously distilling out from the reaction mixture an azeotrope consisting essentially of water and solvent until substantially all the water produced during the reaction has been removed thereby, and, thereafter, crystallizing the product from the remaining solution.

This invention relates to novel N-(N'-methylenepyrrolidonyl)-2-substituted anilines which are useful intermediates in the synthesis of herbicides. The intermediate compounds of the invention have the formula: ##STR1## Where R is alkyl, C.sub.1 -C.sub.6, alkenyl, C.sub.3 -C.sub.5, alkyleneoxyalkyl, --(CH.sub.2).sub.n OR', where n=1-3, and R' is alkyl, C.sub.1 -C.sub.3, and cycloalkyl, ##STR2## where n'=0-3, R' is hydrogen or alkyl, C.sub.1 -C.sub.3, and,

N-(N'-Methylenepyrrolidonyl)-2-substituted anilines

Herbicidal N-(haloacetyl)-N-(N'-methylenepyrrolidonyl)-2-alkoxyanilines are provided in this invention having the formula: ##STR1## where R is alkyl of 1-6 carbon atoms, R' is hydrogen or lower alkyl of 1-3 carbon atoms, and X is halogen. Another feature of the invention is the provision of N-(N'-methylenepyrrolidone)-2-alkoxyaniline or intermediates useful in making such herbicides. These intermediates are prepared by reaction of a 2-alkoxyaniline with an N-methylolpyrrolidone or an N-halomethylenepyrrolidone. The herbicide product than is obtained by acylation of the intermediate with a haloacetyl halide. The compounds of the present invention show good herbicidal activity against grassy weeds.

Herbicidal compounds having the formula: ##STR1## where n is 1-3,

Herbicidal n-(haloacetyl)-n-(n-methylene

The invention provides broad spectrum herbicidal diacylimide compositions which include compounds having the formula: ##STR1## where R and R' are selected from alkyl, alkenyl, haloalkyl and haloalkenyl having from 1-5 carbon atoms, being the same or different groups. The compositions of this invention show excellent agricultural herbicidal activity, particularly against foxtail millet, Japanese millet, crabgrass and pigweed, and aquatic herbicidal activity against lower and higher submerged aquatic plants.

Broad spectrum herbicidal diacylimide compositions

The invention provides broad spectrum herbicidal diacylimide compositions which include compounds having the formula: ##STR1## where R and R' are selected from alkyl, alkenyl, haloalkyl and haloalkenyl having from 1-5 carbon atoms, being the same or different groups. The compositions of this invention show excellent agricultural herbicidal activity, particularly against foxtail millet, Japanese millet, crabgrass and pigweed, and aquatic herbicidal activity against lower and higher submerged aquatic plants. The diacylimide compounds generally are prepared by reacting a suitable amide with an acyl halide. The acyl halide precursor may be prepared, if necessary, from the corresponding acid by reaction with a suitable halogenating agent, such as thionyl chloride. Similarly, a given amide may be readily prepared, for example, from the corresponding acyl halide by reaction with ammonia.

Aquatic herbicidal diacylimide compositions

Herbicidal compounds having the formula: ##STR1## where N=0-3,

Herbicidal N-(haloacetyl)-N'-methylenepyrrolidonyl)-2-cycloalkoxyanilines

Insecticidal N-acyl-N-(N'-methylenepyrrolidonyl)dialkylanilines having the formula: ##STR1## where R.sub.1 and R.sub.2 are both lower alkyl, and R is alkyl, alkenyl or haloalkenyl. Are prepared by two-step process involving reaction of 2,5-dialkylaniline with N-methylolpyrrolidone followed by acylation. The compounds of the present invention show good insecticidal activity against the Mexican bean beetle.

Insecticidal N-methylpyrrolidinonylacetanilides

The invention provides broad spectrum fungicidal diacylimide compositions which include compounds having the formula: ##STR1## where R and R' are selected from alkyl, alkenyl, haloalkyl and haloalkenyl having from 1-5 carbon atoms, being the same or different groups. The compositions of this invention show excellent agricultural fungicidal activity, particularly against bean rust, rice spot, tomato blight and other agricultural pathogens. The diacylimide compounds generally are prepared by reacting a suitable amide with an acyl halide. The acyl halide precursor may be prepared, if necessary, from the corresponding acid by reaction with a suitable halogenating agent, such as thionyl chloride. Similarly, a given amide may be readily prepared, for example, from the corresponding acyl halide by reaction with ammonia.

Growing community of inventors

Elizabeth, NJ, United States of America

Louis Schneider